How to Travel Boston like a Local

Boston Massachusetts is my hometown. If you haven’t thought about traveling to New England, it should be on your list and Boston should be your first stop. I’m proud to be a “Mass-hole” as we’re called and I’m sure anyone else from the area would say the same.

Boston doesn’t care what you think. We not trying to be New York, LA, or Miami. Boston is a small city that packs a punch. Because of that, as a traveler you can see and do a lot in a short amount of time. I’ve been spending my days bartending giving advice to tourists, so I’m passing that advice on to you, my friends!
Let’s start with getting around..  It’s called the “T” or the train. For better or worse, the different colored lines of the MBTA travel from under ground to street level. Be sure to grab a CharlieCard. As I write this, a one way fare is $2.25 with a Charlie Card and $2.75 without. The MBTA could use some TLC but it’s reasonably reliable and will get you to where you want to be.

As a mentioned, Boston is a small city. Which means most of the T Stops are actually walking distance from one another. If it’s a nice day, walk! Boston is historical and really beautiful. If you see a red line painted on the ground- follow it. You’re on the Freedom Trail, which is the walking route you can walk for free or take a tour of. It will take you to all the best historical sites of the American Revolution.

The only thing we could be more proud of than our city’s past, is our current Sports teams. Bostonians have been fortunate enough to have several celebratory championship parades within recent years. Boston is affectionately known to those who live there as “ Title Town” and on that note let’s make one thing clear. Nobody wants to hear you talk shit about Tom Brady. Your point is moot, and people will get angry.  The Red Sox-Yankee rivalry still exists but I think only for the sake of tradition at this point. In my lifetime, I’ve seen the transition from chants of “ Yankees Suck” to “ F**k Goddell”. Haha..yeah…we’re a colorful bunch.

If you travel like I do and you’re in Boston, you’ll quickly realize our annoyingly strict liquor laws. We’re not kidding when we say, Boston does not have happy hours and pouring doubles is technically illegal. Despite this, drinking remains a huge part of Boston culture. Since I’ve spent my time deeply connected with Boston’s restaurant industry culture, I’d like to consider myself as an expert in this category.  With out further adieu, here are the bars to be at.

Nothing I love more than Brunch.. if you fall into this category you should check out The Friendly Toast in Back Bay. Sit at the bar and tell them Dana sent you. Nobody is doing the brunch and full bar thing better in town….

But now that I’ve shamelessly plugged a previous employer.. Also check out Daryl’s in the South End for some real good southern cooking accompanied by AMAZING live jazz/ funk/ soul music. Totally worth it.

Dive Bars, you say?
Corner Pub, Biddy Early’s, Bukowskis, Durty Nelly’s
The Silhouette, Model, The Avenue

Good Grub, Low key atmosphere?

Deep Ellum/ Lone Star, LuLu’s Allston,  De Lux, Lincoln, Boston Burger Company, Naco Taco, BatteryPark, CitySide

Irish

Boston has a large “we’re wicked Irish culture”. There are plenty of Irish pubs. Off the top of my head, Mcgreevy’s, LIR, Bell in Hand, The Burren, JJ Foley’s, The Black Rose 

College Bars with possible sticky dance floors
Scholars, Tavern in the Square Allston ( affectionally referred to as TITS), The Greatest Bar, Coogins, Patrons, The Tam. This category really isn’t my cup of tea, but to each their own.

Oh you Fancy, huh?

Tavern Road, Top of the Hub (on top of the Prudential Center) , Strega, Deuxrue, Tamezcal, The Daily Catch,

In general, you should wander around the North end for Italian food, wine and dessert. It’s super quaint and lively all year round. Do not drive in the area unless you want to have a panic attack before your cannoli.

The quintessential tourist traps that you should probably at least check of briefly :

Faneuil Hall / Quincy Market- There will be street performers and stores you’ve seen 100 times. But Quincy Market is an indoor food mecca. You will be overwhelmed by the choices- I always suggest going through the whole thing once before purchasing anything.

Duck Tours-  OKAY! Duck Tours will definitely mark you as a tourist however, they are super informative and really fun. Plus, you drive right into the Charles river from the Street. The Duck Boats are retired war vessels.

The Boston Commons/ The Fens/ The Esplanade –  These are all beautiful parks and areas to walk around. You will see beautiful gardens, great skylines and who doesn’t love a nice afternoon walk. Granted, you probably will want to do as little walking as possible if for some crazy reason you WANTED to come to Boston in the winter.

Boylston St & Newbury St-  Great shopping and restaurants, big Brownstones and the rich people who can afford to live in the area walking their cute dogs. This is the Copley Square area of Boston and where the Boston Marathon Finish Line is every April.

Cambridge- Technically speaking, Cambridge is a different city than Boston and it definitely has it’s own thing going on. Ever heard of Harvard, or MIT? Cambridge is eclectic and after living there myself for two years.. I am willing to bet on your visit you will be amazed by the people and things you see on the street. If you spend enough time there you will understand what it means when someone says “ only in Cambridge”. It’s worth checking out the Harvard Square and Central Square areas.

Good things To Know

  • For anyone making the move to Boston…NEVER drive a large Uhaul or anything like it on Storrow Dr (low bridges) .
  • Pack for multiple types of weather especially if it’s spring or fall. It’s completely normal to have a 30 degree Monday and a 75 degree Tuesday (that’s Fahrenheit folks). The saying of the New England climate goes, “if you don’t like the weather, wait a minute”. As for summer and winter, expect humid heat and freezing snow,respectively.
  • We don’t say hi to strangers passing on the street
  • There is absolutely no rhythm or reason for the street layout. Massachusetts residents are commonly known for aggressive driving and from a local, driving around Boston is a challenge. If you’re not comfortable driving, I’d save the rental car for when you want to head to the Cape.

Like I said, Boston is my hometown and I could talk all day about it,so I’d love to give you more insight. Any travelers have other favorite spots? Let me know!